Cyclohexanecarboxylic acid → HCID 20541088, compound

HRID 1065026Notes

Reaction equation

Br.[Br:2][C:3]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][CH:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:7]=2[CH:6]=[C:5]([O:22][CH3:23])[C:4]=1[O:24][CH3:25].[CH:26]1([C:32](O)=O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[BH4-].[Na+]>>[Br:2][C:3]1[C:13]2[CH2:12][CH2:11][N:10]([CH2:32][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:9][CH:8]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[C:7]=2[CH:6]=[C:5]([O:22][CH3:23])[C:4]=1[O:24][CH3:25]

Participants

Reactant 3

HCID 7413Cyclohexanecarboxylic acid

HCID 4311764Sodium borohydride

HCID 12624819HCID 12624819, compound

Product 1

HCID 20541088HCID 20541088, compound

Procedure

6-Bromo-7,8-dimethoxy-1-(p-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (3 g) is reacted with cyclohexylcarboxylic acid in the presence of sodium borohydride as in Example 1 to give 6-bromo-3-cyclohexylmethyl-7,8-dimethoxy-1-(p-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine base and, after treatment with boron tribromide, 6-bromo-3-cyclohexylmethyl-7,8-dihydroxy-1-(p-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide.

Sources & evidence

ORD record: ord-e0f9b5d6d1554fd7ab6d5707a437b590
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04328153

Reaction notes

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